The Brooklyn 100: Josh Gondelman, Writer and Comedian

Even if you haven’t personally experienced the aura of kindness that beams forth from Gondelman’s presence, you’ve probably read one of his hilarious tweets, or experienced his humor as one of the writers on John Oliver’s Last Week Tonight. The world of comedy has lately faced down specters of abuse, but Gondelman is a reminder that good guys exist even in the darkest places, and his determination to shine in word and deed has not gone unnoticed, or unappreciated.

When did you first start getting into comedy? When did you first consider yourself “successful” in comedy… was there a landmark or milestone that was especially meaningful to you?
I’ve always loved comedy as a spectator, and I acted in and wrote funny plays in high school. In college, I started doing improv and sketch, and after my freshman year I got into standup in and around Boston. I don’t know if I consider myself “a success” but I definitely feel like I’m “doing okay.” I try to appreciate little steps forward. Whether it was doing my first paid gig or getting staffed to write for a show or booking a late night set. So there’s never been a goal of “If I do this I will have made it.” It’s always been one foot in front of the other and trying to get better.

What advice do you have for comedians and comedy writers who are just starting out?
The Conan O’Brien maxim of working hard and being nice always applies. Plus, find the stuff you like to do and the people you like to do it with. Make work you’re proud of and put it in a place where people can see it. I think that’s both true and vague enough that I’ve covered all my bases.

When did you first begin writing for John Oliver and what has your experience been like there?
I came on to run all the show’s digital stuff before the premiere in 2014, and I started writing for the show about a year later at the beginning of season two. It’s been wonderful! Such a great opportunity to learn from and work with incredibly talented, kind, hard-working people.

Obviously writing jokes for somebody else is completely different from performing them yourself. What are the pros and cons of each, and how does it change your writing style when you’re writing for someone else versus yourself?
Writing for myself is fun because I can do whatever I want, and I don’t have to fit anyone else’s sensibility. Writing for others is great because it means I’m part of a project that’s bigger than just me and generally better than something I could do on my own. That’s incredibly gratifying.

How does writing jokes for social media/Twitter change your style? Since it’s a fairly new outlet in the history of comedy, do you think it’s more helpful or distracting for emerging comedians?Writing for social media–Twitter specifically–is fun, but it rewards incomplete jokes and easily relatable images and ideas. It can be super helpful in terms of practicing writing and putting your voice in the world, but it’s also not a one-to-one of any other kind of writing. So unless your goal is to write only tweets forever, you’ve got to do other stuff too.

You just released your second comedy album, Physical Whisper, what is that process like?
It’s great! It’s so nice to have a way to share an hour of standup when I’m not able to travel and say it to people in person. It’s a long period of getting material ready, then a live show to record. Then there’s some editing and figuring out the album art. Now I’m in the waiting period which is exciting, but the least fun. Tom Petty was for sure right about that.

What’s the funniest joke you’ve ever told?
Oh boy. I honestly don’t know if any joke I’ve ever told was as funny as the time when I was like 14 I was playing hide and go seek tag in a friend’s neighborhood, and as I was running away, I ducked between two trees, and realized too late there was a thin chain link fence between them. I fell onto my back in the yard, and my friends saw me from down the street just dive into the trees and fall backwards out of them. As I landed I wheezed: “Fence!” as an explanation. I still have a scar on my arm from the…you know…fence. That’s real commitment to a bit (a bit I didn’t know I was doing at the time). I don’t think I’ll ever be as funny on purpose as I was that night by accident.

Have you ever completely bombed a show/joke? How did you recover?
Yes for sure absolutely! I think the way I get through a bombed joke and an entire bombed show are very similar. Admit to myself what is happening, but proceed undeterred and with the appearance of confidence. It helps you recover from a joke that doesn’t work and also helps you not quit comedy after a brutal show. You have to be incredibly self-aware so you improve but also you have to look like you don’t know anything’s wrong.

Do you have advice for people who are super intimidated or nervous about doing comedy in person? Do you think the internet is a good middle ground for that?
Sure! The worst thing that will happen (in person) is a bad show. And, geologically speaking, those are so insignificant they may as well never happen. I think internet stuff can help, but again, it’s not the same as live performing, so if that’s what you want to do, just do it! It’ll be bad and then get better (or you’ll stop, which is okay too). My general advice is to do the thing closest to what you want to be doing. So if you want to act in sketches, shooting videos is a helpful way to start. But standup can’t be approximated with just writing.